Monthly Rentals in Wailea-Makena

Discover long-term rentals that feel like home for stays of a month or longer.

Nearby monthly rentals

Guest favorite
Condo in Wailea
4.93 out of 5 average rating, 167 reviews

Stunning ocean view! 2/2 in the heart of Wailea

VinceRating, 5 stars2 months ago
I couldn't recommend Pat & Jim's condo enough. It was extremely clean and well-kept. Pat was extremely communicative and all instructions were super helpful and proactive. It felt like home immediately. The only downside, which is not unique to this condo, but I would guess applies to many condos in the Ekolu development, and probably other similar properties elsewhere in Wailea, is that it was a bit noisy. I'm an extremely light sleeper and, especially during the winter months at home, I am used to very quiet nights. Traffic and nature noises were significant for me at night, so I did have some difficulty sleeping. But this is just something to keep in mind if you're considering any condo in Wailea - as I said, it is not a unique feature of Pat & Jim's condo. If you're used to noise and/or are a heavy sleeper, this is absolutely, without question, the condo for you!
Guest favorite
Condo in Kihei
4.95 out of 5 average rating, 57 reviews

Wailea Hidden Gem

JeanneRating, 5 stars1 week ago
We truly enjoyed our stay in Donna's unit. Besides being beautifully decorated and comfortable, the unit was immaculate, extremely well stocked in terms essentials such as kitchen items, bedding, beach accessories, bathroom accessories, and laundry. Parking was directly in front of the unit and the unit was an easy walk to the pool. We would not hesitate to book again in the future.
Guest favorite
Condo in Wailea
4.97 out of 5 average rating, 165 reviews

Wailea Gem-Remodeled Ocean View

MargaretRating, 5 stars2 weeks ago
The location can't be beat and the condo grounds are stunning. The patio gets beautiful sunset views. Comfortable bed & having a 2nd bathroom is really nice.
Guest favorite
Condo in Kihei
4.93 out of 5 average rating, 122 reviews

Newly Remodeled 1bed/1bath, Kihei/Wailea

LisaRating, 5 stars3 months ago
Very nice place within walking distance to beaches and an easy quick drive to many restaurants

Amenities and perks for longer stays

Furnished rentals

Fully furnished rentals include a kitchen and the amenities you need to live comfortably for a month or longer. It’s the perfect alternative to a sublet.

Flexibility you need

Choose your exact move-in and move-out dates and easily book online, without any additional commitment or paperwork.*

Simple monthly prices

Special rates for long-term vacation rentals and a single monthly payment without additional charges.*

Book with confidence

Reviewed by our trusted community of guests and 24/7 support during your extended stay.

Work-friendly spaces for digital nomads

Traveling professional? Find a long-term stay with high-speed wifi and dedicated working spaces.

Looking for corporate housing?

Airbnb has fully furnished apartment homes ideal for staffing, corporate housing, and relocation needs.

Stay near Wailea-Makena's top sights

Wailea Beach35 locals recommend
Kamaole Beach Park II201 locals recommend
Cafe O'Lei Kihei241 locals recommend
Monkeypod Kitchen by Merriman240 locals recommend
The Shops at Wailea222 locals recommend
Polo Beach11 locals recommend

Destinations to explore

*Some exclusions may apply in certain geographies and for some properties.
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